Synthesis of some pyrazolylaldehyde N-isonicotinoyl hydrazones and 2,5-disubstituted 1,3,4-oxadiazoles as DNA photocleaving agents

被引:8
作者
Kumar, M. [1 ]
Kumar, V. [1 ]
Beniwal, V. [2 ]
机构
[1] Maharishi Markandeshwar Univ, Dept Chem, Mullana 133207, Ambala, India
[2] Maharishi Markandeshwar Univ, Dept Biotechnol, Mullana 133207, Ambala, India
基金
英国科研创新办公室;
关键词
Pyrazole; Oxadiazole; Hydrazone; Isonicotine; DNA photocleavage; (Diacetoxyiodo)benzene; BIOLOGICAL EVALUATION; PYRAZOLE DERIVATIVES; NATURAL-PRODUCTS; DESIGN; THIAZOLES; BASE; ACID;
D O I
10.1007/s00044-015-1340-x
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
In search of potential biologically active compounds, some novel 2,5-disubstituted 1,3,4-oxadiazole derivatives have been prepared conveniently via oxidation of newly synthesized pyrazolylaldehyde N-isonicotinoyl hydrazones by (diacetoxyiodo)benzene in dichloromethane under mild reaction conditions. Compounds were obtained in excellent yields, and their structures have been established on the basis of their FT-IR, H-1, C-13 NMR, and mass spectral data. The DNA photocleavage potential for all the synthesized compounds was evaluated using agarose gel electrophoresis. It has been observed that oxadiazole derivatives showed a significant level of DNA photocleavage activity when compared with their corresponding hydrazones, and some modifications in the basic structure may lead to construct some potential chemotherapeutic agents in future.
引用
收藏
页码:2862 / 2870
页数:9
相关论文
共 50 条
  • [41] Propylphosphonic anhydride (T3P®): an efficient reagent for the one-pot synthesis of 1,2,4-oxadiazoles, 1,3,4-oxadiazoles, and 1,3,4-thiadiazoles
    Augustine, John Kallikat
    Vairaperumal, Veeramani
    Narasimhan, Sharmila
    Alagarsamy, Padma
    Radhakrishnan, Anbarasi
    TETRAHEDRON, 2009, 65 (48) : 9989 - 9996
  • [42] A novel synthesis of 2,5-disubstituted 1,3,4-oxadiazolines by the regioselective cyclization of 1,4-disubstituted thiosemicarbazides
    Feng, Dexin
    Huang, You
    Chen, Ruyu
    Yu, Yaqin
    Song, Haibin
    SYNTHESIS-STUTTGART, 2007, 12 (12): : 1779 - 1784
  • [43] Green synthesis, molecular docking and in vitro biological evaluation of novel hydrazones, pyrazoles, 1,2,4-triazoles and 1,3,4-oxadiazoles
    Younis, Ahmed
    Kassem, Asmaa F.
    Aboulthana, Wael M.
    Sediek, Ashraf A.
    SYNTHETIC COMMUNICATIONS, 2024, 54 (22) : 1984 - 2002
  • [44] Synthesis of 3,5-Disubstituted 1,2,4-Oxadiazoles from Amidoximes and Aldehydes in the Superbasic System NaOH/DMSO
    A. A. Shetnev
    V. E. Pankratieva
    A. S. Kunichkina
    A. S. Vlasov
    I. K. Proskurina
    A. D. Kotov
    M. K. Korsakov
    Russian Journal of Organic Chemistry, 2020, 56 : 1181 - 1186
  • [45] Synthesis of 3,5-Disubstituted 1,2,4-Oxadiazoles from Amidoximes and Aldehydes in the Superbasic System NaOH/DMSO
    Shetnev, A. A.
    Pankratieva, V. E.
    Kunichkina, A. S.
    Vlasov, A. S.
    Proskurina, I. K.
    Kotov, A. D.
    Korsakov, M. K.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 56 (07) : 1181 - 1186
  • [46] SYNTHESIS OF SOME NEW 2-(SUBSTITUTED-PHENYL)-5-(N,N-DIPHENYLAMINOMETHYL)-1,3,4-OXADIAZOLES: A SAFER ANTI-INFLAMMATORY AND ANALGESIC AGENTS
    Kataria, Aditya Kumar
    Khan, Suroor Ahmad
    Alam, Mohammad Mumtaz
    Husain, Asif
    Akhtar, Mymoona
    Khanna, Suruchi
    Haider, Rashid
    Shaquiquzzaman, Mohammad
    ACTA POLONIAE PHARMACEUTICA, 2011, 68 (03): : 381 - 386
  • [47] A NEW EFFICIENT ONE-POT SYNTHESIS OF 2,5-DIARYL-1,3,4-OXADIAZOLES
    Chiriac, Constantin I.
    Tanasa, Fulga
    Nechifor, Marioara
    REVUE ROUMAINE DE CHIMIE, 2011, 56 (12) : 1113 - +
  • [48] Synthesis and antioxidant evaluation of some new 2-benzoylamino-5-hetaryl-1,3,4-oxadiazoles
    Bondock, Samir
    Adel, Shymaa
    Etman, Hassan A.
    RESEARCH ON CHEMICAL INTERMEDIATES, 2016, 42 (03) : 1845 - 1861
  • [49] Synthesis and pharmacological activities of some new 5-substituted-2-mercapto-1,3,4-oxadiazoles
    Desai, Shobha R.
    Laddi, U.
    Bennur, Rajani S.
    Patil, P. A.
    Bennur, S.
    INDIAN JOURNAL OF PHARMACEUTICAL SCIENCES, 2011, 73 (05) : 116 - 119
  • [50] Synthesis of N-Sulfonyl Amidines and 1,3,4-Oxadiazoles through Electrochemical Activation of DMF
    Mahanty, Kingshuk
    Halder, Atreyee
    De Sarkar, Suman
    ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (01) : 96 - 103